title: Stereoselective synthesis of 2-acetamido-1,2-dideoxyallonojirimycin (DAJNAc), a new potent hexosaminidase inhibitor.
abstract: A practical synthesis of the previously unreported N-acetyl-D-allosamine glycomimetic DAJNAc is described. The reaction sequence involves Pd-catalyzed allylic substitution by phthalimide in an azaheterobicyclic scaffold as the key step. The new iminosugar resulted in being a stronger β-N-acetylglucosaminidase (human placenta) competitive inhibitor than the D-gluco (DNJNAc) and D-galacto (DGJNAc) stereoisomers.
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), Barcelona, Spain.
authors.forename: Alex
authors.initials: A
authors.lastname: de la Fuente
authors.forename: Ruben
authors.initials: R
authors.lastname: Martin
authors.forename: Teresa
authors.initials: T
authors.lastname: Mena-Barragán
authors.forename: Xavier
authors.initials: X
authors.lastname: Verdaguer
authors.forename: José M
authors.initials: JM
authors.lastname: García Fernández
authors.forename: Carmen
authors.initials: C
authors.lastname: Ortiz Mellet
authors.forename: Antoni
authors.initials: A
authors.lastname: Riera
mesh_terms: D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005260:Female; D006596:Hexosaminidases / Q000032:analysis* / Q000737:chemistry*; D006801:Humans; D011247:Pregnancy; D013237:Stereoisomerism; D001619:beta-N-Acetylhexosaminidases / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C586052:2-acetamido-1,2-dideoxyallonojirimycin; D017485:1-Deoxynojirimycin; D006596:Hexosaminidases; D001619:beta-N-Acetylhexosaminidases